Cas no 459423-16-6 ((4-methoxy-3-phenylphenyl)boronic acid)

(4-Methoxy-3-phenylphenyl)boronic acid is a versatile boronic acid derivative widely used in Suzuki-Miyaura cross-coupling reactions, a key method for forming carbon-carbon bonds in organic synthesis. Its methoxy and phenyl substituents enhance electronic and steric properties, improving reactivity and selectivity in aryl-aryl coupling processes. This compound is particularly valuable in pharmaceutical and materials science research, where precise functionalization of aromatic systems is required. It exhibits good stability under standard conditions and demonstrates compatibility with a range of catalysts and substrates. The product is typically supplied with high purity, ensuring reliable performance in demanding synthetic applications. Proper handling under inert atmospheres is recommended to maintain its integrity.
(4-methoxy-3-phenylphenyl)boronic acid structure
459423-16-6 structure
Product Name:(4-methoxy-3-phenylphenyl)boronic acid
CAS No:459423-16-6
MF:C13H13BO3
MW:228.051523923874
CID:3398553
PubChem ID:21037383
Update Time:2025-10-29

(4-methoxy-3-phenylphenyl)boronic acid Chemical and Physical Properties

Names and Identifiers

    • BORONIC ACID, (6-METHOXY[1,1'-BIPHENYL]-3-YL)-
    • Boronic acid, B-(6-methoxy[1,1'-biphenyl]-3-yl)-
    • (4-methoxy-3-phenylphenyl)boronic acid
    • 3-phenyl-4-methoxyphenyl boronic acid
    • OODAYTYTMKXJFO-UHFFFAOYSA-N
    • (6-Methoxy-[1,1'-biphenyl]-3-yl)boronic acid
    • EN300-1457870
    • B-(6-Methoxy[1,1'-biphenyl]-3-yl)boronic acid
    • DB-415701
    • 459423-16-6
    • (6-METHOXY-3-BIPHENYLYL)BORONIC ACID
    • SCHEMBL5828211
    • (6-METHOXY-3-BIPHENYLYL)BORONICACID
    • Inchi: 1S/C13H13BO3/c1-17-13-8-7-11(14(15)16)9-12(13)10-5-3-2-4-6-10/h2-9,15-16H,1H3
    • InChI Key: OODAYTYTMKXJFO-UHFFFAOYSA-N
    • SMILES: B(C1C=CC(OC)=C(C2=CC=CC=C2)C=1)(O)O

Computed Properties

  • Exact Mass: 228.0957744Da
  • Monoisotopic Mass: 228.0957744Da
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 17
  • Rotatable Bond Count: 3
  • Complexity: 229
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 49.7?2

(4-methoxy-3-phenylphenyl)boronic acid Pricemore >>

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Additional information on (4-methoxy-3-phenylphenyl)boronic acid

Recent Advances in the Application of (4-Methoxy-3-phenylphenyl)boronic Acid (CAS: 459423-16-6) in Chemical Biology and Pharmaceutical Research

The compound (4-methoxy-3-phenylphenyl)boronic acid (CAS: 459423-16-6) has emerged as a versatile building block in chemical biology and pharmaceutical research. This boronic acid derivative has garnered significant attention due to its unique structural features, which enable diverse applications in drug discovery, materials science, and chemical biology. Recent studies have explored its potential as a key intermediate in the synthesis of bioactive molecules, particularly in the development of proteolysis-targeting chimeras (PROTACs) and boron-based therapeutics.

In the context of drug discovery, (4-methoxy-3-phenylphenyl)boronic acid has demonstrated remarkable utility in Suzuki-Miyaura cross-coupling reactions, a cornerstone of modern medicinal chemistry. A 2023 study published in the Journal of Medicinal Chemistry highlighted its use in the synthesis of novel kinase inhibitors, where the boronic acid moiety served as a crucial handle for constructing biaryl systems with enhanced target specificity. The electron-rich aromatic system of this compound appears to contribute to improved pharmacokinetic properties of the resulting drug candidates.

The compound's role in boron neutron capture therapy (BNCT) has also been investigated. Researchers at Kyoto University recently reported (2024) on the development of boron-containing amino acid analogs incorporating (4-methoxy-3-phenylphenyl)boronic acid as tumor-targeting agents. The methoxy-phenyl substitution pattern was found to significantly influence cellular uptake and retention in cancer cells, suggesting potential applications in precision oncology approaches.

From a chemical biology perspective, (4-methoxy-3-phenylphenyl)boronic acid has shown promise in the development of activity-based probes for glycosidases and other carbohydrate-processing enzymes. A Nature Chemical Biology publication (2023) detailed its incorporation into fluorescent sensors capable of real-time monitoring of enzymatic activity in live cells. The compound's ability to reversibly interact with diols makes it particularly valuable for studying carbohydrate metabolism in disease states.

Recent advances in materials science have also leveraged this boronic acid derivative. A 2024 ACS Applied Materials & Interfaces paper described its use in the fabrication of stimulus-responsive hydrogels for controlled drug delivery. The pH-dependent binding properties of the boronic acid group enabled the creation of smart materials capable of glucose-triggered insulin release, with potential applications in diabetes management.

In conclusion, (4-methoxy-3-phenylphenyl)boronic acid (CAS: 459423-16-6) continues to demonstrate remarkable versatility across multiple research domains. Its unique chemical properties and biological compatibility position it as a valuable tool in the development of next-generation therapeutics and diagnostic agents. Future research directions may focus on expanding its applications in targeted drug delivery systems and as a component of novel biomaterials.

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